Record Information
Version2.0
Creation Date2012-05-31 13:59:09 -0600
Update Date2015-09-13 12:56:13 -0600
Secondary Accession Numbers
  • ECMDB03431
Identification
Name:L-Histidinol
Description:L-Histidinol is a structural analogue of the essential amino acid L-histidine. It is an intermediate in histidine metabolism. It is converted to L-histidinal via bifunctional histidinal dehydrogenase/histidinol dehydrogenase (EC:1.1.1.23). (KEGG)
Structure
Thumb
Synonyms:
  • (S)-b-amino-1H-Imidazole-4-propanol
  • (S)-beta-Amino-1H-imidazole-4-propanol
  • (S)-β-amino-1H-Imidazole-4-propanol
  • Histidinol
  • Histidol
  • HSO
  • Imidazole C-4(5) deriv. 4
  • L-histidinol
Chemical Formula:C6H11N3O
Weight:Average: 141.171
Monoisotopic: 141.090211989
InChI Key:ZQISRDCJNBUVMM-YFKPBYRVSA-N
InChI:InChI=1S/C6H11N3O/c7-5(3-10)1-6-2-8-4-9-6/h2,4-5,10H,1,3,7H2,(H,8,9)/t5-/m0/s1
CAS number:4836-52-6
IUPAC Name:(2S)-2-amino-3-(1H-imidazol-5-yl)propan-1-ol
Traditional IUPAC Name:HSO
SMILES:N[C@H](CO)CC1=CN=CN1
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic nitrogen compounds
Sub ClassOrganonitrogen compounds
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • 1,2-aminoalcohol
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Primary aliphatic amine
  • Alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility129.0 mg/mLALOGPS
logP-1.3ALOGPS
logP-1.7ChemAxon
logS-0.04ALOGPS
pKa (Strongest Acidic)13.45ChemAxon
pKa (Strongest Basic)9.41ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area74.93 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.19 m3·mol-1ChemAxon
Polarizability14.74 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Secondary Metabolites: Histidine biosynthesisPW000984 Pw000984Pw000984 greyscalePw000984 simple
histidine biosynthesisPW000810 Pw000810Pw000810 greyscalePw000810 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
13± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
19± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
20± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0udi-1970000000-5f8fce52ae008e9577d3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0udi-1960000000-2bd5915e1e2204265b30View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0udi-0960000000-04ea4478dfe81318bf5cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0fk9-9540000000-9d5008be3cb2086af6f4View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-03di-5900000000-b7271e5101b1cf971b24View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udi-1970000000-5f8fce52ae008e9577d3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udi-1960000000-2bd5915e1e2204265b30View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udi-0960000000-04ea4478dfe81318bf5cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0fk9-9540000000-9d5008be3cb2086af6f4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-03e9-9800000000-eb7ec98ac413a4a5067dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-006x-1900000000-c360dc1772243d0c7ccaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-eba5a77ea4a62d8375f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-009922321d7904037f80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-0900000000-3a563827d1023d4dadd7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00e9-7900000000-4baa9781af4596ef1a49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9000000000-98f4a65357b52f544e0cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9000000000-5921f5ed9c6159fbe48eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-9000000000-a7a82388a3feef766362View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0089-8900000000-b7fa72e4e20dbc5d79d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-3a563827d1023d4dadd7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00e9-7900000000-4baa9781af4596ef1a49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-98f4a65357b52f544e0cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-5921f5ed9c6159fbe48eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-128590ab44ecade57be8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0089-8900000000-b7fa72e4e20dbc5d79d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0900000000-e19200b81166dd2ceb6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abc-3900000000-8073bbe0237addc54c81View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5a-9300000000-a833e6da71592c915e87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-f2eb428fd58c551e9f84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0596-9800000000-7dcca6b55761d69a3dc2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9100000000-4649be9a2b45a85f4de1View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Raju RV, Datla RS, Warrington RC, Sharma RK: Effects of L-histidine and its structural analogues on human N-myristoyltransferase activity and importance of EEVEH amino acid sequence for enzyme activity. Biochemistry. 1998 Oct 20;37(42):14928-36. Pubmed: 9778369
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • Warrington RC, Cheng I, Zhang L, Fang WD: L-histidinol increases the vulnerability of cultured human leukemia and lymphoma cells to anticancer drugs. Anticancer Res. 1993 Nov-Dec;13(6A):2107-12. Pubmed: 8297120
  • Warrington RC, Norum JN, Hilchey JL, Watt C, Fang WD: A simple, informative, and quantitative flow cytometric method for assessing apoptosis in cultured cells. Prog Neuropsychopharmacol Biol Psychiatry. 2003 Apr;27(2):231-43. Pubmed: 12657362
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Beltra, A. P.; Bonete, P.; Gonzalez-Garcia, J.; Garcia-Garcia, V.; Montiel, V. Electrochemical synthesis of L-histidinol using solvated electrons. Journal of the Electrochemical Society (2005), 152(4), D65-D68.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16255
HMDB IDHMDB03431
Pubchem Compound ID165271
Kegg IDC00860
ChemSpider ID144886
Wikipedia IDNot Available
BioCyc IDHISTIDINOL
EcoCyc IDHISTIDINOL

Enzymes

General function:
Involved in catalytic activity
Specific function:
D-erythro-1-(imidazol-4-yl)glycerol 3- phosphate = 3-(imidazol-4-yl)-2-oxopropyl phosphate + H(2)O
Gene Name:
hisB
Uniprot ID:
P06987
Molecular weight:
40278
Reactions
D-erythro-1-(imidazol-4-yl)glycerol 3-phosphate = 3-(imidazol-4-yl)-2-oxopropyl phosphate + H(2)O.
L-histidinol phosphate + H(2)O = L-histidinol + phosphate.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the sequential NAD-dependent oxidations of L- histidinol to L-histidinaldehyde and then to L-histidine
Gene Name:
hisD
Uniprot ID:
P06988
Molecular weight:
46110
Reactions
L-histidinol + H(2)O + 2 NAD(+) = L-histidine + 2 NADH.